CN105713025B - A kind of electroluminescent organic material, preparation method and its manufactured luminescent device - Google Patents
A kind of electroluminescent organic material, preparation method and its manufactured luminescent device Download PDFInfo
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- CN105713025B CN105713025B CN201610051237.1A CN201610051237A CN105713025B CN 105713025 B CN105713025 B CN 105713025B CN 201610051237 A CN201610051237 A CN 201610051237A CN 105713025 B CN105713025 B CN 105713025B
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- 239000011368 organic material Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 16
- QQLPPRIZUPEKMV-ZHACJKMWSA-N 2-[(e)-2-phenylethenyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1/C=C/C1=CC=CC=C1 QQLPPRIZUPEKMV-ZHACJKMWSA-N 0.000 claims abstract description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000011701 zinc Substances 0.000 claims abstract description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 14
- 238000005401 electroluminescence Methods 0.000 claims description 12
- 235000005074 zinc chloride Nutrition 0.000 claims description 12
- 239000011592 zinc chloride Substances 0.000 claims description 12
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 10
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- -1 polytetrafluoroethylene Polymers 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000000935 solvent evaporation Methods 0.000 claims description 4
- 239000010405 anode material Substances 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000010189 synthetic method Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 4
- 235000019441 ethanol Nutrition 0.000 abstract description 3
- 230000001681 protective effect Effects 0.000 abstract description 2
- 241001025261 Neoraja caerulea Species 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 238000004528 spin coating Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000001455 metallic ions Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000013110 organic ligand Chemical group 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- YRPYTFXEHXXYQW-UHFFFAOYSA-N 2-ethenyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C=C)=NC2=C1 YRPYTFXEHXXYQW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- NTRPDBRJGBMHQP-UHFFFAOYSA-N terbium(4+) Chemical compound [Tb+4] NTRPDBRJGBMHQP-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of electroluminescent organic material, preparation method and its manufactured luminescent device, the molecular formula of the material are as follows: Zn (C15H12N2)2Cl2.A kind of electroluminescent organic material of the present invention, synthesis and its manufactured device provide a kind of blue-ray organic electroluminescent material dichloro two (2- styryl benzimidazole) and close zinc (II), synthetic method and the device using the preparation of this kind of material.Electroluminescent organic material thermal stability with higher has preferable dissolubility in ethyl alcohol, chloroform, increases the type of the electroluminescent organic material for the coloured light that turns blue.Synthetic method is using anhydrous methanol as solvent, and using solvent-thermal method, reaction condition is mild, and solvent anhydrous methanol can recycle, and synthesis process is environmentally protective.
Description
Technical field
The present invention relates to field of material technology more particularly to a kind of electroluminescent organic material, preparation method and its it is made
Luminescent device.
Background technique
1963, Pope etc. anthracene single crystal two sides apply voltage, observed organic electroluminescent phenomenon (M.Pope,
H.Kallmann,P.Magnante,Electroluminescence in organic crystals.Chemical
Physics,1963,38:2042-2043.).But difficult and device drive voltage is high, they are adopted since organic single-crystal is grown
Technique practicability is poor.1987, C.W.Tang et al. use ultra-thin membrane technology, using 8-hydroxyquinoline aluminum complex as
Luminescent layer is prepared for the luminescent device of sandwich type, greatly using indium tin oxide films and metal alloy as anode and cathode
Amplitude reduces the driving voltage of device, while improving light emission luminance (C.W.Tang, S.A.Vanslyke, Organic
electroluminescent diodes,Applied Physics Letters,1987,51(12):913-915.).This
Breakthrough makes the research of organic electroluminescent cause the extensive concerns of scientific and technological circle.
Organic electroluminescent is a kind of novel display technology.Organic electroluminescence device is one kind by multilayer organic film
The electroluminescent device of formation, organic film can use vacuum evaporation, deposition or spin coating proceeding and formed on substrate.Organic Electricity
Luminous efficiency, service life etc., performances were mainly determined by luminescent material in electroluminescence device.
Application of the new material in organic electroluminescence device is the power for pushing electroluminescent technology to make constant progress.
In recent years, the material of a large amount of function admirables makes organic electroluminescent achieve some breakthrough progress.
Recently, as organic electroluminescent is before the huge application that total colouring and solid-state white lighting area are shown
Scape, organic electroluminescent technology have obtained extensive research and concern.Pass through rare earth ion europium (III) and terbium (IV) itself
4f-4f transition, a large amount of feux rouges and green light material have obtained good application in terms of organic electroluminescence device.It is relatively above-mentioned
Material, blue light material of the launch wavelength in 400-490nm are relatively fewer.
Metal organic complex because its structure diversity and adjustability, luminescent material, in terms of
There is important potential using value.The photoluminescent property of metal organic complex, the molecule with central metallic ions and organic ligand
Structure has relationship.The metallic ion coordination of different organic ligand and phasor, may issue the fluorescence of different wave length.2- benzene
The complex dichloro two (2- styryl benzimidazole) that vinyl benzimidazole and zinc chloride are formed close zinc (II) have compared with
Big rigid plane skeleton, good thermal stability, while there is the features such as synthetic method is simple, and yield is high.The complex exists
The blue light that wavelength is 452nm can be issued under ultraviolet excitation.Two 2- styryl benzimidazole ligand moleculars are via one
Zn2+It connects, makes that energy transmission can occur between ligand-ligand of intramolecular, to improve luminous efficiency.Benzo miaow
Styryl on azoles 2 belongs to electron donating group, so that the conjugacy of ligand is strong, complexes stability enhancing, meanwhile, benzene second
The introducing of alkenyl is so that the dissolubility enhancing of Zn complex in organic solvent, complex has preferable in ethyl alcohol, chloroform
Dissolubility.In the preparation process of device, the method that spin-coating film method forms a film instead of vacuum evaporation or vacuum deposition can be used.
Summary of the invention
It is an object of the invention to solve the problems of the above-mentioned prior art, a kind of organic electroluminescent chemical combination is provided
Object, synthetic method and the organic electroluminescence device comprising the compound.
A kind of electroluminescent organic material, molecular formula are as follows: Zn (C15H12N2)2Cl2, structural formula is as follows:
The preparation method of electroluminescent organic material as described above, comprising the following steps:
(1) 2- styryl benzimidazole and zinc chloride are weighed, is dissolved in a certain amount of anhydrous methanol respectively, under stirring
The methanol solution of zinc chloride is added dropwise in the methanol solution of 2- benzene alkenyl benzimidazole, is stirred evenly；
(2) mixed solution prepared by step (1) is transferred in the reaction kettle that liner is polytetrafluoroethylene (PTFE), reaction kettle is sealed
It is good, it is put into the baking oven that temperature is 60-120 DEG C and reacts 12-48h, then take out rear cooled to room temperature, solvent evaporation is removed
Light yellow solid powder crude product is obtained after going, product can be obtained in chloroform and acetone recrystallization.
Preferably, method as described above, in step (1), the mass ratio of 2- styryl benzimidazole and zinc chloride is
3.0~3.6:1.
Preferably, method as described above, zinc chloride used are free of the crystallization water.
Preferably, method as described above, in step (2), it is poly- four that mixed solution prepared by step (1), which is transferred to liner,
In the reaction kettle of vinyl fluoride, after reaction kettle is sealed, it is put into the baking oven that temperature is 100 DEG C and reacts for 24 hours.
A kind of organic electroluminescence device, including the anode material, emitting layer material and cathode material stacked gradually；Wherein
The emitting layer material is to be prepared using electroluminescent material prepared by method as described above.
A kind of electroluminescent organic material of the present invention, synthesis and its manufactured device provide a kind of blue light organic electroluminescence hair
Luminescent material dichloro two (2- styryl benzimidazole) closes zinc (II), synthetic method and the device using the preparation of this kind of material
Part.Electroluminescent organic material thermal stability with higher has preferable dissolubility in ethyl alcohol, chloroform, increases
Turn blue coloured light electroluminescent organic material type.Synthetic method, using solvent-thermal method, reacts item using anhydrous methanol as solvent
Part is mild, and solvent anhydrous methanol can recycle, and synthesis process is environmentally protective.
Detailed description of the invention
Fig. 1 is that dichloro two (2- styryl benzimidazole) prepared by embodiment 1 closes zinc (II) infrared spectrogram；
Fig. 2 is the luminescent spectrum figure of organic electroluminescence device prepared by embodiment 4.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, the technical solution below in the present invention carries out clear
Chu is fully described by, it is clear that described embodiments are some of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
Embodiment 1
0.44 gram of 2- styryl benzimidazole and 0.14 gram of zinc chloride are weighed, is dissolved in 10mL anhydrous methanol, stirs respectively
It mixes and the methanol solution of zinc chloride is added dropwise under state in the methanol solution of 2- benzene alkenyl benzimidazole, stir evenly；It will be upper
It states mixed solution to be transferred in 100 milliliters of reaction kettles that liner is polytetrafluoroethylene (PTFE), reaction kettle is sealed, being put into temperature is 100 DEG C
Baking oven in reaction for 24 hours, then take out rear cooled to room temperature, by solvent evaporation remove after obtain light yellow solid powder
0.49 gram, chloroform is 0.45 gram with product after acetone recrystallization, and the methanol evaporated is 19.5mL.
Embodiment 2
0.87 gram of 2- styryl benzimidazole and 0.27 gram of zinc chloride are weighed, is dissolved in 15mL anhydrous methanol, stirs respectively
It mixes and the methanol solution of zinc chloride is added dropwise under state in the methanol solution of 2- benzene alkenyl benzimidazole, stir evenly；It will be upper
It states mixed solution to be transferred in 100 milliliters of reaction kettles that liner is polytetrafluoroethylene (PTFE), reaction kettle is sealed, is put at a temperature of 90 °C
28h is reacted in baking oven, then takes out rear cooled to room temperature, obtains light yellow solid powder 0.97 after solvent evaporation is removed
Gram, product is 0.91 gram after chloroform and acetone recrystallization, and the methanol evaporated is 29.3mL.
Embodiment 3
[ITO/PEDOT:PSS/ dichloro two (2- styryl benzimidazole) closes zinc (II)/Alq to luminescent device3/LiF/
Al]
In the glove box full of high pure nitrogen, the first spin coating one in the glass substrate for being coated with ITO (tin indium oxide) anode
Layer hole injection layer PEDOT:PSS (poly- (3,4-rthylene dioxythiophene)-polystyrolsulfon acid) (50nm), then on the layer
Emitting layer material (30nm) described in one layer of embodiment 1 of spin coating, then vacuum evaporation electron transfer layer Alq3(8-hydroxyquinoline
Aluminium) (20nm), electron injection material LiF (0.5nm), cathode material Al (150nm), the starting voltage of the device is 3.5V, bright
It spends up to 9300cd/m2。
Embodiment 4
[ITO/PEDOT:PSS/ dichloro two (2- styryl benzimidazole) closes zinc (II)/Alq3/LiF/ to luminescent device
Al]
In the glove box full of high pure nitrogen, one layer of hole injection of first spin coating in the glass substrate for be coated with ito anode
Layer PEDOT:PSS (50nm), the then emitting layer material (30nm) described in one layer of embodiment 2 of spin coating above this layer, then
Vacuum evaporation electron transfer layer Alq3(20nm), electron injection material LiF (0.5nm), cathode material Al (150nm), the device
Starting voltage be 3.5V, brightness is up to 9460cd/m2。
Fig. 1 is that dichloro two (2- styryl benzimidazole) prepared by embodiment 1 closes zinc (II) infrared spectrogram.
Fig. 2 is the luminescent spectrum figure of organic electroluminescence device prepared by embodiment 4.The position of emission peak in 452nm,
Half-peak breadth is 80.4nm.
Each functional group in absorption peak position description in the infrared spectrogram of Fig. 1 product ligand of synthesis, mainly
The product for illustrating synthesis is target product.Manufactured organic electroluminescence device hair is mainly illustrated in the luminescent spectrum figure of Fig. 2
The shape of spectrum out, the position of emission peak, luminous intensity, half-peak breadth etc..The light that device made of illustrating issues is blue
Coloured light.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although
Present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: it still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features；
And these are modified or replaceed, technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution spirit and
Range.
Claims (6)
1. a kind of electroluminescent organic material, which is characterized in that its molecular formula are as follows: Zn (C15H12N2)2Cl2, structural formula is as follows:
2. a kind of preparation method of electroluminescent organic material described in claim 1, which comprises the following steps:
(1) 2- styryl benzimidazole and zinc chloride are weighed, is dissolved in a certain amount of anhydrous methanol respectively, by chlorine under stirring
The methanol solution for changing zinc is added dropwise in the methanol solution of 2- styryl benzimidazole, stirs evenly；
(2) mixed solution prepared by step (1) is transferred in the reaction kettle that liner is polytetrafluoroethylene (PTFE), reaction kettle is sealed, is put
Enter and react 12-48h in the baking oven that temperature is 60-120 DEG C, then takes out, cooled to room temperature, after solvent evaporation is removed
To light yellow solid powder crude product, product is can be obtained in chloroform and acetone recrystallization.
3. according to the method described in claim 2, it is characterized in that, in step (1), 2- styryl benzimidazole and zinc chloride
Mass ratio be 3.0~3.6:1.
4. according to the method described in claim 2, it is characterized in that, zinc chloride used is free of the crystallization water.
5. according to the method described in claim 2, it is characterized in that, the mixed solution of step (1) preparation is turned in step (2)
Enter in the reaction kettle that liner is polytetrafluoroethylene (PTFE), after reaction kettle is sealed, is put into the baking oven that temperature is 100 DEG C and reacts for 24 hours.
6. a kind of organic electroluminescence device, which is characterized in that including the anode material, emitting layer material and cathode stacked gradually
Material；Wherein the emitting layer material be electroluminescent organic material prepare using claim 2 the method prepare and
At.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1302302A (en) * | 1999-03-31 | 2001-07-04 | Lg化学株式会社 | Organometallic complex molecule and organic electroluminescent device using the same |
| CN1781340A (en) * | 2003-02-27 | 2006-05-31 | 株式会社丰田自动织机 | Organic electroluminescent device |
| CN1815774A (en) * | 2004-12-13 | 2006-08-09 | 株式会社丰田自动织机 | Organic el devices |
| CN101165137A (en) * | 2007-10-19 | 2008-04-23 | 中山大学 | Zinc complex luminescent material |
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2016
- 2016-01-26 CN CN201610051237.1A patent/CN105713025B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1302302A (en) * | 1999-03-31 | 2001-07-04 | Lg化学株式会社 | Organometallic complex molecule and organic electroluminescent device using the same |
| CN1781340A (en) * | 2003-02-27 | 2006-05-31 | 株式会社丰田自动织机 | Organic electroluminescent device |
| CN1815774A (en) * | 2004-12-13 | 2006-08-09 | 株式会社丰田自动织机 | Organic el devices |
| CN101165137A (en) * | 2007-10-19 | 2008-04-23 | 中山大学 | Zinc complex luminescent material |
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